IMAP, Gmail, and Apple Mail can be a powerful combination, but all have certain idiosyncrasies that can test your patience. Joe Kissell offers an in-depth exploration of the three technologies and how to use them together optimally.Show full article

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For the past few months, I've been unusually happy with my overall email situation. I won't say it's perfect, but it's way better than it has been in the past - much better even than when I was running my own mail server on my own Xserve, a setup that I would have thought offered me the ultimate in flexibility and power. The ingredients I now rely on - Google's Gmail (via Google Apps Standard Edition, which lets me use my own domain name), IMAP, and Apple Mail - provide the sweet spot that best suits my needs. However, as I discovered through a considerable amount of trial and error, the recipe needed to combine all these ingredients into an edible dish was anything but obvious. For those who have had less-than-satisfactory experiences with their email providers and software (especially Gmail and Apple Mail, respectively), I'd like to share how I achieved my personal state of email satisfaction.

Well, that's what I intended to do, anyway. The more I wrote, the more I realized how many aspects of the IMAP/Gmail/Mail universe are unclear or confusing, as evidenced by the many email messages I've received on those subjects, and as feedback to my books ("Take Control of Apple Mail in Leopard" and "Take Control of Spam with Apple Mail") and my Macworld articles on the topic. So, what I thought would be a straightforward article has turned into a manifesto. (That means it's quite long, and somewhat opinionated - fair warning!) And, I admit it: I've written it for a largely selfish reason, which is to save myself from having to explain this information repeatedly in email messages! But I do hope you'll find it interesting and helpful if you've ever struggled with the combination of IMAP, Gmail, and Mail.

I want to be clear about one thing right up front: my method works well for me because it matches the way I use, and think about, email. If you're accustomed to using or thinking about email in a much different way, your mileage may vary - and you may find my setup unworkable. In particular, if you expect Mail (or any IMAP client) to work just like Gmail's Web interface in the way it handles archiving, some of what I describe here may disappoint you. Email management is a matter of, among other things, habit and taste. So I don't presume to say this system will work for everyone, or that it doesn't have limitations.

That warning aside, I'm going to - eventually - explain how I do what I do in what I hope is a clear, systematic way. In order to provide context for the actual steps to take, I'm going to begin with detailed background information about IMAP generally and the somewhat nonstandard ways Mail and Gmail handle it. Feel free to skip the background stuff and jump ahead to "How to Configure Everything for Maximum Happiness," but even highly knowledgeable users may find this material enlightening.

IMAP -- I've been extolling the virtues of IMAP (Internet Message Access Protocol) for well over a decade, and although this protocol has become much more popular during that time, it's clear that a lot of people still don't understand what it is and why it's superior to POP (Post Office Protocol). Even in the past couple of months I've heard more than one person dismiss IMAP using arguments that reflect basic misunderstandings. So, without giving a complete, detailed technical overview of IMAP, let me lay out the basics.

POP and IMAP are both methods of retrieving messages from a mail server. (In fact, many mail servers support both protocols, enabling you to access the same messages in either way.) The most common way to explain the difference between POP and IMAP is this: With POP, you download all your messages to your computer, whereas with IMAP, all your messages remain on the server. That's more or less true, but it overlooks several important points.

• First, the fact that IMAP stores messages on the server is often taken to imply that it's equivalent to the POP option to download messages but leave them on the server. But it's much different. In the first place, IMAP servers, unlike POP servers, can keep track of flags for each message, indicating things like which messages have been read, forwarded, or replied to. With POP, your local email client has to track this information. That means if you download a bunch of messages on computer A using POP but leave them on the server, and then switch to computer B, you can still download the messages again, but they'll all appear to be unread - computer B won't know which messages you've seen, filed, or otherwise dealt with, because that information isn't kept on the POP server.
• Second, speaking of filing, another key difference between POP and IMAP is that POP has just one mailbox - your inbox - on the server, whereas an IMAP server can have any number of mailboxes. So, if you check your email on computer A and move a certain message to your Read mailbox, and then check your email on computer B, that message will appear in the Read mailbox there as well.
• Third, I would like to put to bed, once and for all, the biggest IMAP myth of all time. It is not the case that when you use IMAP, you can access your email messages only when you're connected to the Internet! I want to be crystal clear about this. If you use IMAP, you absolutely can have local copies of all your email messages, in their entirety, on your computer, and you can read, search, file, and do anything else you want to do with those messages even if you have no Internet connection at all - just as you can when you use POP. It is true that in some IMAP clients, this behavior isn't automatic and requires a few clicks to set up, but there's nothing about IMAP that inherently prevents messages from living both on your hard disk and on the server. In fact, the most common configuration of IMAP these days - and the default configuration in Mail - is to have one's local mail store exactly mirror the server's mail store, such that changes made on one side are reflected automatically on the other side. File a message locally, it's filed on the server; delete a message locally, it's deleted on the server, and so on.

In short, although both POP and IMAP can get email messages from a server onto your screen, IMAP provides a much broader and richer set of options. And, as a bonus, you can use IMAP as a sort of rudimentary email backup. Even if your disk crashes or your computer is stolen, you'll still have a copy of all your messages on the server. (The reverse is also true: if your IMAP provider should lose any of your messages, you'll have a local backup.) One of the things I've appreciated most in my years of using IMAP is that I can switch email clients, computers, or even operating systems without giving the slightest thought to exporting or importing email messages (and all the grief that can involve). I simply enter my account credentials in the new software and (not counting the time it takes to download new local copies of my existing messages) I'm all set.

IMAP does have a couple of downsides, which may or may not be significant to you. First, most IMAP servers impose a storage quota on each user. If that quota is fairly low (say, 1 GB), you could run out of space for all your messages, forcing you to move some off the server to a mailbox that's stored only on your computer. (Gmail deals with this problem by setting generous quotas, which increase in size every day, and by offering even larger quotas for a modest annual fee.) Also, if you have a slow Internet connection (such as a dial-up or GPRS mobile connection), IMAP can be slower than POP because your client must explicitly ask the server for each message you want to download, rather than simply downloading whatever new messages appear in the inbox automatically. (With fast Internet connections, this method of asking for and receiving data isn't a problem.)

Mail and IMAP -- Although IMAP is wonderful in theory, all IMAP servers are not created equal. Some have features that others lack, or use nonstandard approaches to providing one capability or another. In addition, one's experience of using IMAP is always mediated by client software (either software you run locally on your computer or software that provides a Web-based interface to the IMAP server). Unfortunately, many IMAP clients also take certain liberties with the IMAP protocol, with the result being that some of that wonderfulness is lost from the user's perspective. Apple Mail, which is a much better IMAP client than some, nevertheless has a handful of quirks in its handling of IMAP that can drive one to distraction. If you combine Mail's IMAP oddities with those of a less-than-standard IMAP server - Web Crossing, I'm looking at you - you could easily have unpleasant experiences that may lead you to the erroneous conclusion that IMAP itself is buggy or poorly designed. (Later on, I'll get into the even weirder ways that Gmail deals with IMAP.)

Here are some of the problematic ways in which Mail handles IMAP:

• Mail has had, for quite some time, odd performance problems when communicating with at least some brands of IMAP server. Frequently, the simple act of checking one's mail takes an inordinately long time, sometimes because Mail, in the background, is busy synchronizing a bunch of mailboxes and only gets around to checking your inbox when it has completed a number of other tasks. For the same reason, it's not uncommon for Mail to take a long time to quit. It looks like nothing is happening, but in fact it's trying (clearly, not hard enough) to log out of certain accounts, finish syncing mailboxes, or do other last-minute cleanup tasks such as deleting old messages. Some Mail users never encounter these problems, but if you're unlucky enough to use an uncooperative IMAP server - and especially if you use Mail for several accounts at once - Mail can appear to be quite sluggish when using IMAP.
• IMAP supports server-side searching (say that five times fast), but Mail doesn't. Mail relies on a Spotlight index of (the locally cached copies of) all your messages to deliver search results. For all the hype Apple has heaped on Spotlight, I (and many other Mac users) have found it to be a drag, even in Leopard. It's often slow and frequently yields incomplete results. And even though system-wide Spotlight searches are reasonably capable, Mail's pathetic search interface has no support for Boolean operators or proximity searches, and can't search hidden headers, HTML source, or any other message components that are normally invisible in the user interface. This is a pity, because IMAP itself supports all this - if Mail let you tie into the server's existing search capabilities, you might get faster, more accurate, and more flexible results.
• With most IMAP clients (including, notably, Entourage), you can subscribe to particular mailboxes in a given IMAP account, meaning only those mailboxes show up in the client's mailbox list. If you have old mailboxes full of archived mail, for example, you can opt not to subscribe to them, so your software never has to waste time syncing them, searching them, or whatever. Mail doesn't do subscriptions - it just shows you all your mailboxes, all the time. If you choose Get Account Info from the pop-up Action menu at the bottom of the sidebar in Mail and click Subscriptions, you might think you'll see a list of mailboxes to which you can subscribe or unsubscribe. But usually this list is blank; it shows only mailboxes in "Public" or "Shared" mailboxes on the server, if such mailboxes exist.
• When it comes time to delete a message, the IMAP procedure is for your client to set a flag on the server that marks the message as ready for deletion. Then, at some later point, your client (manually or automatically) tells the server to "expunge" the mailbox - that is, actually delete all the messages in it that are marked for deletion. In the meantime, the client can hide the marked-for-deletion messages, or show them in a strikethrough style, or designate them as almost gone in some other way. Mail, instead, tries to replicate the Finder's model for deleting files. When you delete a message, Mail appears to move it to a Trash mailbox (which, confusingly, may be either local or on the IMAP server, depending on settings that aren't obvious). Then, to delete the message for good, you choose Mailbox > Erase Deleted Messages > Account-Name. However, in reality, what happens when you delete a message in Mail is the following. First, Mail makes a copy of the message in your Trash mailbox. Then it marks the existing copy for deletion, making it invisible in the process. As far as your IMAP server is concerned, the message is still where it always was, only with a new flag. When you choose Erase Deleted Messages, Mail expunges the original copy and deletes the copy in the Trash mailbox. You can fiddle with Mail's preferences to treat deleted messages in a more standard IMAP manner, but it takes some doing.
• By convention, most IMAP servers and clients set aside special mailboxes for Drafts, Sent, Junk, and Trash, but the names used for each of these mailboxes differ from one program to another. Mail lets you designate any IMAP mailbox to serve any one of these purposes (by using commands on the Mailbox > Use This Mailbox For submenu). However, after you set up a new IMAP account, the first time you send a message, Mail looks for a mailbox named Sent Messages to store a copy in. If it doesn't find that mailbox, it creates it. (Similarly, when you first save a draft or delete a message, Mail looks for a Drafts mailbox or Deleted Messages mailbox, and if it doesn't find one with that exact name, it creates one. And, if you use Mail's built-in junk mail filtering to move suspected spam to a server-based Junk mailbox but there's no mailbox there named Junk, Mail creates one.) So, for example, even if you already had a mailbox on your IMAP server called Sent, which you wanted to use to hold sent messages, and even though Mail's mailbox list contains a mailbox called Sent, what happens behind the scenes is that Mail creates a new mailbox on the server called Sent Messages, displays that mailbox using the label "Sent," and uses that to store sent messages - while, at the same time, displaying your existing Sent mailbox separately in the mailbox list! This is incredibly confusing, especially when I have to explain to someone that their Sent mailbox isn't really their Sent mailbox, and that to fix the problem, they have to select the Sent mailbox listed under their IMAP account name, choose Mailbox > Use This Mailbox For > Sent, and then delete the Sent Messages mailbox that will suddenly, mysteriously appear where Sent used to be. Gah!
• The other special attribute of the Drafts, Sent, Junk, and Trash mailboxes is that most IMAP clients (including Mail) let you choose whether you want to store their contents locally only, or on the server (with a local copy). By default, Mail stores all these items except Junk on the server. Personally, I've never seen the point in offering the choice; it seems to me that it would be simpler if these mailboxes were always stored on the server and cached locally, like the rest. Be that as it may, your choice of which of these items are enabled, along with the names used for each mailbox as described in the previous point, can have a big effect on how Mail behaves, but it's complicated for non-expert users to decode what Mail is doing or how to set it up optimally.
• Mail can, and usually does, make as many as four simultaneous connections to any given IMAP server. In theory, this should provide faster performance by enabling Mail to do several different things at once (such as copying messages from one mailbox to another while refreshing the contents of your inbox). However, sometimes all those connections actually slow Mail down, especially when you're checking multiple IMAP accounts at the same time. Moreover, Mail sometimes insists on keeping all four of those connections open even when they're not actively doing anything, and can be very slow to close connections that are stuck or non-responsive for a period of time. This behavior has special implications for Gmail, as I'll explain shortly - and unfortunately, Mail offers no user interface (as some other IMAP clients do) to set the maximum number of concurrent connections or whether to keep those connections perpetually open.

Gmail and IMAP -- Gmail started out as a Web-only interface for email. Since Google had complete control over how email was processed, stored, and presented, they decided to handle it all in the way that made the most sense for their existing indexing infrastructure and for (what they perceived as) users' needs. The basic idea was that a good search engine should make mailboxes obsolete - just toss everything in one big mailbox and do a quick Google search to find whatever you're looking for.

Later, a refinement appeared in the form of user-defined labels. By labeling (or tagging) messages, you could indicate that many seemingly unrelated messages shared something in common, thereby letting you quickly display a group of messages that would never otherwise appear together in a search. Gmail lets you apply as many labels as you want to each message, which is a much different approach to categorization from using mailboxes (since each message can appear in only one location in a mailbox hierarchy).

Users flocked to Gmail for a variety of reasons, not the least of which were its cost (free), its large storage space for email, and its accurate spam filtering. But because many users preferred to use their existing email software, rather than a Web browser, to access their email, Google added a POP interface to Gmail. Obviously, when downloading messages via POP, you lose Gmail's search and labeling features (though you can also choose to leave all the messages on the server as well, to give yourself another way to access them). Through Google Apps, Google even made it possible to use Gmail with one's existing email address, so that users could take advantage of all the nifty Gmail features without having to switch domains or addresses.

Gmail eventually added yet another major feature that many people, including me, had been dying for: IMAP access. For me, the benefits of IMAP outweighed the benefits of Gmail, but I was thrilled when I learned I could get both. Now, I could have all the IMAP goodness (such as freely switching between clients and platforms) along with all the Gmail goodness (excellent spam filtering, a great Web-based interface for when I'm away from Mail, and most of all, freedom from having to constantly futz with my existing and increasingly finicky mail server).

To pull this off, Gmail's paradigm of using multiple labels to categorize messages (with no capability to create mailboxes) had to be reconciled with IMAP's assumption that you can create as many mailboxes as you need. Their solution was to map labels to mailboxes and vice-versa. So, if you move a message in your IMAP client to a mailbox called Stuff, you'll see, in Gmail's Web interface, that the message has a label called Stuff. If, using the Web interface, you apply the labels Apples, Oranges, and Mangoes to a message, then, in your IMAP client, you'll see three copies of that message - one each in the Apples, Oranges, and Mangoes mailboxes. It's not a perfect solution, and it's certainly nonstandard in that IMAP normally stores only one copy of each message - but it's a reasonable design, as far as it goes.

Apart from that unusual system, Gmail's IMAP implementation is weird (at least, from the Mail user's perspective) in other ways. For example, Gmail limits each account to 10 simultaneous IMAP connections, not counting access via the Web. That sounds like a lot, and for many people it isn't a problem. But because Mail is so greedy in this regard - opening, as I mentioned earlier, as many as four connections, and keeping them open - the practical upshot is that you're limited to running just two simultaneous copies of Mail (say, one on your desktop Mac and one on your laptop). Even more aggravating, if I have Mail open on my Mac and my iPhone turned on (whose version of Mail also uses multiple IMAP connections), I've hit my limit right there. If I then open Mail on any of the other Macs I might be using at any given time, that puts me over the limit with just three IMAP clients - Gmail automatically blocks the connection to the most recently used copy of Mail until the total number of connections drops below 10. And, because Mail can take such a very long time to let go of its connections, this may mean a wait of up to 10 minutes (Gmail's IMAP timeout period for inactivity) even after taking one of my copies of Mail offline. (And before you ask, no, this has nothing to do with Mail's "Use IDLE command if the server supports it" checkbox - that's another whole can of worms.) A Gmail engineer who contacted me expressed hope that this problem will be addressed in a future version of Mail.

In addition to the limit of 10 connections, Gmail watches for what it considers excessive activity - such as downloading all your IMAP messages several times in a day. (The need to download all one's messages occurs, for example, when setting up Mail on a new computer or re-syncing Mail's entire database after data corruption.) Although the exact algorithm Gmail uses to determine what's excessive is not publicly known, I've personally surpassed whatever the metric is when, for one reason or another, I had to download all my IMAP messages just twice in one day, not counting my usual IMAP access. When you surpass this mysterious download limit, Gmail locks you out of all IMAP access for up to 24 hours - an extremely unpleasant occurrence.

There are other limitations and issues with Gmail's IMAP support, too, some of which I mention later in connection with Mail.

Mail and Gmail and IMAP -- Mail, by itself, has some issues with any IMAP server, and Gmail, as a nonstandard IMAP server, has some issues with any IMAP client. When you put the two of them together, you can run into some interesting behavior. For example, Gmail's one big mailbox that holds all your messages is called, cleverly enough, All Mail. (This includes copies of messages you've sent, even though they're also available by using the Sent label/mailbox, as well as spam messages and deleted messages in your Trash.) This mailbox, along with all your other labels-as-mailboxes, syncs locally to Mail when you access Gmail via IMAP. As a result, if you (like most IMAP users) have filed all your messages into various mailboxes, Mail would download at least two copies of every single message - the one in All Mail and an additional copy for each label the message had. Of course, this poses no problem to IMAP clients that can unsubscribe from particular mailboxes, but oops! Mail can't do that. This was one of the biggest headaches I had in my early days of using Gmail with Mail, and in just a bit I'll explain how to overcome this problem.

A further complication of All Mail is that Gmail has a concept of "archiving" messages, which means moving them out of your inbox but not necessarily giving them another label. The result of this is that they appear only in the All Mail mailbox. If you prevent All Mail from appearing in Mail (as I recommend and describe ahead), this means you won't see any messages in Mail that you previously archived there using Gmail's Web interface but which lack any other label. Nor does Mail (or IMAP generally) have anything precisely equivalent to Gmail's Archive button - that is, a way to move messages out of the inbox without explicitly putting them somewhere else. This is one of those examples of needing to think about email a certain way: if you're committed to the archiving paradigm, my suggestions won't suit you. However, I present a possible workaround ahead in my detailed list of instructions.

Another source of confusion was what to do with the special mailboxes Drafts, Sent, Junk, and Trash - specifically, whether or not (in view of the odd label/mailbox behavior and the duplication of messages) to store their contents on the server. Google's Web site provided suggested settings, and some other Web sites I read offered conflicting advice. What I discovered was that with Google's recommended Mail settings, every time you send a message you get two copies - one stored in a local Sent mailbox and the other stored in Gmail's Sent Mail mailbox on the server (and, of course, synced locally too)! Only after experimenting with a variety of settings myself and observing the results (in multiple accounts, on multiple Macs) did I arrive at a combination that gave me approximately the behavior I expected, even though it contradicts Google's advice.

And finally, I'm accustomed to having all my mailboxes be part of a single hierarchy within any account. But Gmail wants to display, along with all my regular labels-as-mailboxes, another mailbox called [Gmail] that contains my Drafts, Sent, Junk, and Trash mailboxes - plus All Mail and Starred (equivalent to Mail's Flagged status). According to Google, that unfortunate organization was necessary to support certain nonstandard IMAP clients and work around problems with supporting multiple languages. It offends my aesthetic sensibilities, but I wasn't happy with the workaround I discovered for getting rid of the [Gmail] folder either.

How to Configure Everything for Maximum Happiness -- Hey! Everyone who blew off the last few sections because you weren't interested in background info! This is where you jump back in. I'm going to explain, top to bottom, how to configure everything on both the Gmail side and the Mail side to work the way it does for me, which is to say as good as I can figure out how to make it - and that's pretty darn good in my book. I'm also going to mention a few things that, even in this shiny new world order, aren't quite right - and then wrap up with some observations about the pros and cons of using this method for handling email.

Steps 1-5 are basic Gmail and IMAP configuration. You may have done some of these steps already; if so, please read them over anyway to be sure you've set up things the same way I recommend, and if not, make any necessary changes as you go.

(1) Get a Gmail account. I won't walk you through the process because it's fall-off-a-log simple. However, I do want to reiterate that if you want to use your own, existing domain name with Gmail, you need to go through an entirely different setup process to set up a free Google Apps Standard Edition account. This involves changing some of the DNS settings for your domain name to point to Google's servers. It's not hard, and Google offers clear, detailed directions. But be aware that your Google Apps Gmail account is completely separate from any existing Gmail account you may have - you can't simply assign a new email address to your current account. Apart from the initial account sign-up procedure, all the steps that follow are, with a sole exception (noted ahead), identical for either type of account.

(2) Log in to your Gmail account.

(3) At the top of the window, click the Settings link.

(4) Click the Forwarding and POP/IMAP link.

(5) Select Enable IMAP and click Save Changes.

Steps 6-8 configure a special Gmail Labs feature to minimize IMAP annoyances in Mail:

(6) Only if you're using Google Apps, make sure Gmail Labs is enabled. To do this, make sure you're logged in to Gmail as an administrator of your domain, and click the Manage This Domain link at the top of the Gmail window. Then click Domain Settings. On the General tab (displayed by default), make sure both of the following boxes are checked: Automatically Add New Services When They Become Available and Enable Pre-Release Features. Click Save Changes at the bottom of the window. Then log out of Gmail, log back in, and once again click the Settings link.

(7) Click the Labs link, which should appear under "Settings" to the right of "Web Clips." Scroll down until you see Advanced IMAP Controls and click the Enable checkbox next to it. Then click Save Changes.

(8) Click the Labels link under "Settings." Now, uncheck the Show in IMAP checkboxes for Starred and All Mail. This is essentially the same thing as unsubscribing from these two mailboxes, except that you do it on the server side instead of the client side - it applies to all clients. Crucially, this step avoids having the All Mail mailbox, with its duplicates of every single message you send and receive, clutter up Mail.

As I explained earlier, the downside to this approach, for those who like to use Gmail's Archive button to remove messages from the inbox without putting them in another mailbox, is that you can no longer see archived messages in Mail unless they also have some other label. I never used this archiving method - for me, every message has at least one label (or is in a particular mailbox) - so this problem didn't affect me. But if you're accustomed to Gmail's archiving, you may find that you get equally good results by creating a different catch-all mailbox in Mail, such as "Filed," and simply moving all messages to that mailbox that you'd otherwise archive. Then, in Gmail's Web interface, you can select all the messages in All Mail without any other label and apply the Filed label, which makes them appear in Mail's Filed mailbox. It's not exactly the same as archiving, but it's reasonably similar.

(9) Once again click the Forwarding and POP/IMAP link. This time, check a new setting that was added by enabling the Advanced IMAP Controls. If it's not already selected, select Immediately Expunge Messages When I Mark Them Deleted in IMAP (under "Auto-Expunge") and click Save Changes.

Steps 10-15 set up your Gmail account in Mail:

(10) Open Mail, choose Mail > Preferences, click the Accounts button on the toolbar, and click the + (plus) button at the bottom left.

(11) Enter your name, your full Gmail address, and your Gmail password.

(12) Extremely important: uncheck Automatically Set Up Account, and click Continue. (If you leave that box checked, Mail sets up your account as a POP account, which is not what you want.)

(13) On the Incoming Mail Server screen, choose IMAP from the Account Type pop-up menu. Enter a description of your choice, change the Incoming Mail Server field to imap.gmail.com, make sure the User Name field includes your entire Gmail address, and confirm that your password is filled in. Click Continue.

(14) On the Outgoing Mail Server screen, once again enter a description of your choice, and check Use Only This Server. All of the other settings should already be correct - smtp.gmail.com in the Outgoing Mail Server field, Use Authentication checked, and your user name and password filled in.

(15) Click Continue, review your information, and click Create. Give Mail a few minutes to download your existing messages from Gmail and create mailboxes corresponding to your Gmail labels.

Finally, Steps 16-21 enable Mail to deal correctly with Gmail's special mailboxes. Note that you need not explicitly make any changes to the checkboxes in the Mailbox Behaviors view of Mail's Accounts preference pane, but following these steps results in all four of the "Store __ messages on the server" boxes there being checked.

(16) Look in the mailbox list in Mail's sidebar. You should now see, at the bottom, an account with whatever description you specified for your Gmail account in Step 12. Click the disclosure triangle next to it to display its contents. You'll see, at minimum, a white mailbox (white signifying that the mailbox itself contains no messages) labeled [Gmail], along with mailboxes representing any other labels you've created. Click the disclosure triangle next to [Gmail] to display its contents, which should at this point be Drafts, Sent Mail, Spam, and Trash. (Had you not performed Steps 6-8, you'd also see Starred and All Mail here.)

(17) To tell Mail to use Gmail's Sent Mail mailbox as the Sent mailbox for this account, select Sent Mail under [Gmail] and choose Mailbox > Use This Mailbox For > Sent. The Sent mailbox then disappears from under [Gmail] and reappears near the top of your mailbox list as a sub-mailbox with your Gmail account name under the main Sent item. (Here, and in the steps that follow, note that the special mailboxes appear as sub-mailboxes only if you have at least one other account set up in Mail; otherwise, they'll be the only Drafts, Sent, Junk, and Trash mailboxes that appear.) If, after you do this, a Sent Messages mailbox appears at the bottom of your mailbox list in your Gmail account, select all its contents (if any) and drag them to your main Sent mailbox at the top. Wait a few minutes for the transfer to complete, and then select the Sent Messages mailbox, choose Mailbox > Delete Mailbox, and click Delete. I want to reiterate that this advice differs from what Google suggests, but trust me: this is the way you want to do it, to avoid having duplicate sent messages in different mailboxes.

The result of doing this will be that, whether you send a message from Mail or from the Gmail Web interface, a copy will be stored in the same mailbox - the one Mail calls Sent, and Gmail's Web site calls Sent Mail. Note: Do not CC or BCC yourself on messages you send via Gmail. (That is, choose Mail > Preferences, click Composing on the toolbar, and make sure Automatically Cc/Bcc Myself is unchecked.) It's not necessary, because Gmail saves a copy automatically, and you'll only end up with a duplicate. Note also that Gmail displays in your Sent (Mail) mailbox any spam messages you may have received that were forged so that they appear to have come from your own address! Weird and annoying, but if you delete all your spam messages regularly, nothing to worry about - they disappear from Sent too.

(18) Next comes Drafts. As you did with Sent, select Drafts under [Gmail] and choose Mailbox > Use This Mailbox For > Drafts. The Drafts mailbox then disappears from under [Gmail] and reappears as a sub-mailbox under the main Drafts item. Now, whether you save a draft in Mail or in the Gmail Web interface, it'll show up in the same (Drafts) mailbox. (If you were to skip this step, the next time you composed a message, Mail would create a new, hidden Drafts mailbox that would appear, in Gmail, as a label called [Imap]/Drafts. That introduces yet another layer of complexity I prefer to avoid.) Once again, if, after you do this, a Drafts mailbox appears at the bottom of your mailbox list in your Gmail account, select all its contents (if any) and drag them to your main Drafts mailbox at the top. Wait a few minutes for the transfer to complete, and then select the Drafts mailbox under your Gmail account at the bottom of the list, choose Mailbox > Delete Mailbox, and click Delete.

But, you need to be aware of yet another goofy thing about Gmail and Mail when it comes to drafts. Normally, when you compose a message in Mail, it saves a copy in your Drafts mailbox automatically every 30 seconds as well as whenever you manually click Save as Draft. Each time a new draft is saved, Mail deletes any previous draft of that message (without moving it to a Trash mailbox), so you see only one draft in your Drafts mailbox. But Gmail-over-IMAP behaves differently. When you compose a message in your Gmail account, Mail still saves a copy of your work in progress every 30 seconds, and still deletes any previous draft. However, instead of the previous drafts disappearing altogether, they all show up in your Trash mailbox. As a result, if you spend 10 minutes writing a message in your Gmail account in Mail, you could see 20 drafts of that message in your Trash mailbox! This behavior isn't harmful - just empty your Trash every so often, or use Mail's preferences to set up automatic Trash emptying. But it can be quite a shock to see tons of draft messages in your Trash that you never explicitly created or moved there! A Gmail developer told me that this strange behavior was necessary to work around a bug in certain IMAP clients, and that they may be able to find a better solution in the future.

(19) Now on to Trash. Just as in the last two steps, select Trash under [Gmail] and choose Mailbox > Use This Mailbox For > Trash. The Trash mailbox then disappears from under [Gmail] and reappears as a sub-mailbox under the main Trash item. Now, whether you delete a message in Mail or in the Gmail Web interface, it'll show up in the same (Trash) mailbox. If a Deleted Messages mailbox appears at the bottom of your mailbox list in your Gmail account, select all its contents (if any) and drag them to your main Trash mailbox at the top. Wait a few minutes for the transfer to complete, and then select the Deleted Messages mailbox, choose Mailbox > Delete Mailbox, and click Delete.

(20) Finally, the Junk mailbox. Unlike the other three special mailboxes, Mail doesn't store Junk messages on the server by default, the assumption being that there's no need to waste space on the server with messages you don't want in the first place. But Gmail automatically applies a Spam label to all suspected junk mail, which has the effect of keeping it out of your inbox and putting it in a Spam mailbox when viewed from an IMAP client. In other words, spam is already on the server (and, along with all your other IMAP mail, synced locally to your Mac too), so the question becomes how you want to view and manage it. You have two approaches here, both perfectly valid.

One option is to leave the default settings in place. The result would be that any messages Gmail flags as spam would appear (only) in the Spam mailbox under [Gmail] in your Gmail account. You could then review and delete those messages at your leisure - either in Mail or in the Gmail Web interface. However, if Mail's built-in Junk Mail filter were to catch any additional spam messages from your Gmail account (which does happen from time to time), those messages would either be marked as Junk Mail and left in your inbox, or moved to a Junk mailbox in the "On My Mac" (local) portion of your mailbox list, depending on your preferences. In other words, you'd have to look in two places for suspected junk mail instead of one. On the other hand, since Mail's Junk Mail filter is less accurate than Gmail's, it could be that most of what Mail flags as spam are false positives. If so, you may prefer to use this approach, in which the likeliest false positives are all together in a relatively short list that's easy to scan, instead of mixed in with all the other messages that are more likely to be spam.

The other option, and my personal preference, is to go ahead and let Mail treat Gmail's Spam label/mailbox as the Junk mailbox for that account. This has no effect on the number of spam messages downloaded to your computer. What it does change is putting all the junk mail in one place and eliminating an extra mailbox - so I like it for the sake of tidiness. In addition, it means that whenever Mail marks a message as spam by moving it to the Junk mailbox, it also tells Gmail that the message is spam, helping to improve Gmail's spam filtering for all users at the same time Gmail helps to improve Mail's junk mail filtering by teaching it which messages it thinks are spam.

To set up the Junk mailbox in the way I prefer, first choose Mail > Preferences, click Junk Mail, and make sure the Enable Junk Mail Filtering box is checked. Under "When junk mail arrives," if the top radio button (Mark As Junk Mail, but Leave It in My Inbox) is selected, instead select Move It to the Junk Mailbox and click Move. Next, go back to the main Mail window, select Spam under [Gmail], and choose Mailbox > Use This Mailbox For > Junk. The Spam mailbox then disappears from under [Gmail] and reappears as a sub-mailbox under the main Junk item. Now, whether Gmail flags a message as spam, or Mail's Junk Mail filter does, or you manually mark a message as spam in either place, it'll show up in the same mailbox - the one Mail calls Junk, and Gmail's Web site calls Spam. If a Junk mailbox appears at the bottom of your mailbox list in your Gmail account, select all its contents (if any) and drag them to your main Junk mailbox at the top. Wait a few minutes for the transfer to complete, and then select the Junk mailbox, choose Mailbox > Delete Mailbox, and click Delete.

(21) That's (pretty much) it. At this point, your mailbox list should show, under your Gmail account, an empty mailbox called [Gmail] (though it'll contain a mailbox called Spam if you went for the first option in Step 19), along with mailboxes representing your Gmail labels. You can simply ignore the [Gmail] mailbox.

But maybe you can't ignore [Gmail]. Maybe its very presence in your mailbox list offends your sense of order, since it serves no purpose now. Can you get rid of it? Well, you can, but you may find the consequences of doing so even more unpleasant.

To get rid of [Gmail], tell Mail to treat the [Gmail] mailbox, rather than your inbox, as the root of your IMAP account. To do this, choose Mail > Preferences, click Accounts on the toolbar, and select your Gmail account in the list on the left. Click Advanced, and in the IMAP Path Prefix field, type [Gmail]. Then close the Preferences window and click Save. What happens at this point is that [Gmail] disappears - yay! But something else disappears, too: the rest of your Gmail mailboxes! With this configuration, Mail can display only mailboxes that are in the [Gmail] hierarchy. So, let's say you create a new mailbox in Mail called Archives. When you go to the Gmail Web interface, you'll see a new label called [Gmail]/Archives! Only labels that begin with [Gmail]/ will show up as IMAP mailboxes in Mail (or any other IMAP client). This won't affect your Drafts, Sent, Junk, and Trash mailboxes because they were already under [Gmail], but it will mean that if you had messages in any other mailboxes, you'll have to manually relabel them in Gmail in order to make them show up in Mail - and you'll have to live with every Gmail label starting with [Gmail]/. Personally, this bothers me more than having an empty [Gmail] mailbox, but you can do it if you want.

Further Considerations -- Now then. Let me explain what we have at this point. Your email arrives at Gmail's servers and gets filtered for spam automatically. You can then check your email in Mail (or in any other IMAP client, on any computer), or via the Gmail Web interface, and no matter how you look at it, you'll always see the same messages, with the same status (read/unread, replied to, etc.), in the same location (mailbox or label). You have tons of email storage space, access to a boatload of optional (and sometimes experimental) Gmail features, and you're not paying a cent for it.

One thing I love about using Gmail for mail is server-based rules (which Gmail calls filters). To set up a filter, just go to the Gmail Web interface, click the Create a Filter link next to the search field at the top of the window, and follow the instructions. Although Gmail's filters are less sophisticated and flexible than Mail's, I've been able to replicate about 90 percent of the functionality I had with Mail's filters (which I then deleted). Not only does this make Mail snappier by giving it less to do, it means that if I access my messages on the Web, on my iPhone, or in another client, they're already (mostly) presorted into the mailboxes of my choice, and my inbox isn't cluttered with nonessential mail.

Because your mail is hosted by Google's massive server farm, it's not subject to the kinds of problems that could affect mail hosted on a single server (like my Xserve) and is somewhat less vulnerable to outages than with most email providers. But Gmail has had a few (well-publicized) outages (see, for example, "Gmail Outage Marks Sixth Downtime in Eight Months" at PC World from February 2009). Some of these outages have lasted an uncomfortably long time, and they could potentially happen again. Of course, any email provider can have outages - that goes for MobileMe (see "MobileMe Mail and Gmail Go Down Simultaneously," 2008-08-11), Fastmail.fm (see Glenn Fleishman's blog post "No Longer Recommending Fastmail.fm" from August of 2006), and your own server too. My own feeling on the matter is that I'd rather have one of the world's largest Internet companies worrying about my email outage than having to deal with it myself (or leaving it in the hands of a smaller, less-capable email provider), and since I have several other email accounts I can use as a backup, I don't lose too much sleep over it.

Nevertheless, I do, naturally, counsel you to back up the local copies of all your mail. In the event that a catastrophic outage at Google resulted in some or all of your messages disappearing from the server, you want to be sure you have another copy somewhere. So, you know the drill: read the book (or the other book), set up your backups, and test them regularly.

If you have more than one email account (and who doesn't these days?), you can use Gmail as a central repository - either forwarding your other accounts' mail to Gmail or letting Gmail check the messages in other accounts using POP. This lets all your accounts take advantage of Gmail's spam filtering and other features, and is especially helpful for devices like the iPhone that don't offer a consolidated inbox view for multiple accounts. What makes Gmail especially good as a central clearing house (as opposed to, say, MobileMe Mail) is that it offers a way to let you send outgoing mail from other addresses. I describe this entire process in detail in a Macworld article titled "Streamline E-mail with Gmail."

Last but not least, I'd like to put in a plug for the method of email organization I've found to be most effective and least stressful, which is to adopt a strategy that keeps one's inbox empty nearly all the time. As I type these words, there happen to be two messages in my inbox, and that's only because I'm not wired for multitasking and I haven't had a chance to deal with them yet. They'll be gone within the hour. If you want to read about (a simplified version of) how I pull this off despite receiving gazillions of messages every day, see my Macworld article "Empty Your Inbox."

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Ever include the wrong person in an email message to a group? Gmail can now help you out, with a new Google Labs feature that alerts you when it appears you've included an erroneous recipient.Show full article

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Google has added yet another feature to Gmail to protect against inadvertent mistakes. While it lacks the entertaining premise of the Mail Goggles, the new feature, named "Got the wrong Bob?", will likely prove popular with anyone who frequently writes to groups of people.

Once activated, "Got the wrong Bob?" alerts you if it thinks you've included an unusual recipient in the group to which you're writing a message. By keeping tabs on the groups you most often write to, Gmail becomes your eagle-eyed friend, alerting you when you've likely mixed up two similarly named contacts.

For example, if you were hosting a dinner with a regular gang of friends and wanted to invite your buddy Mike, but inadvertently included your obnoxious co-worker Mike instead, Gmail would double check with you to make sure you had the right Mike. A small alert under the address field pops up with the text, "Did you mean: X instead of Y"? Clicking X's name automatically plugs X's email address in the "To:" field, and removes the incorrect contact's address from it.

Don't become too dependent on these alerts; the feature works only when writing to three or more people, and thus you'll still have to pay attention when corresponding with one or two colleagues.

"Got the wrong Bob?" is a nice complement to an older Gmail feature that suggests additional recipients to a group email message when you may have left someone out. That feature, formerly referred to as "Suggest more recipients," has been renamed "Don't forget Bob." (Though I personally would have preferred "What About Bob?".)

To activate either feature, log into your Gmail account, click the beaker icon in the upper right hand corner, scroll down, and click the Enable radio button for "Got the wrong Bob?" or "Don't forget Bob." (If the beaker doesn't appear, click the Settings link and then click the Labs link.) Then click the Save Changes button at the bottom.

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Google’s Gmail. In this first of a multi-part series, he explains why he chose Gmail and what some of the pros and cons are. Future installments will explore the ins and outs of Google’s free mail service.Show full article

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For the record, it has now been some time since I used Eudora 6.2.4 as my everyday email program, and I have instead switched to Google’s Gmail. I realize that may come as a surprise, considering that I wrote the “Eudora Visual QuickStart Guide” back in 1997 and was long a vocal supporter of the program. But Eudora had started crashing more frequently and corrupting mailboxes in the process. I could fix the damaged mailboxes (see “How to Fix Corrupt Eudora Mailboxes,” 4 April 2008), but doing so had become an annoying interruption when I just wanted to move forward with the day’s work.

I held onto Eudora as long as I could because I liked the way the program worked. I liked the fact that it was tweaky and customizable, that it reported clearly what it was doing, and that it was entirely straightforward. I’ve used and written about most other Mac email programs over the years, and if I was forced to generalize, I’d say that they all feel to me as though they’re starting from the same conceptual base as Eudora, but with a different set of priorities. Since I had become utterly familiar with Eudora’s mindset, all these other programs simply felt like awkward take-offs.

That’s why, when it came time to choose a new email program a while back, I picked Google’s Gmail. Alone among my choices at the time, Gmail’s engineers decided to rethink the entire concept of email, throwing out many basic assumptions and designing from scratch. I felt that if I were going to make a major leap (and since email is my primary communication medium, it truly is a huge leap for me), I wanted to develop a new and better way of working, not merely adjust my old habits to a new program that lacked the parts of Eudora I liked.

The classic email program, Eudora included, takes its architectural cues from the stereotypical 1950s office environment, where incoming mail arrives in a single location, is routed according to various rules, and ends up in a single destination where, after being read and potentially replied to, it will be filed away in a hierarchical filing system or deleted. This approach is functional, but many of the advances in email programs over the last few years have been aimed at making it easier to deal with a large influx of mail, easier to file messages, and easier to find them after they’ve been filed. In other words, these changes are simply trying to build robots into the 1950s office environment so everything moves faster. Meanwhile, the world has moved on from those days of secretaries taking dictation from snazzily suited executives.

Gmail’s engineers instead focused their efforts on search, a far more modern concept. After all, Google’s skyrocketing fortunes gave some indication that search was a winning idea. With search at its core and Google’s unimaginably massive server farms backing it up, Gmail could do some seemingly simple things that standalone email programs have been either unable or unwilling to do, most notably trading the old “folder” concept for a modern “label” approach and generating every collection of messages via a search.

As an aside, I’m quite depressed that only Google has been able to do this successfully. I see no reason that a modern Mac couldn’t offer the same level of functionality, and the fact that Gmail can be made to work offline via Google Gears shows that it should be possible. That said, I don’t use Gears; it was flaky last I tested it, and if I don’t have Internet access, there’s not much I can do anyway, since most of my work requires more than just the capability to read and write email.

The other reason I chose Gmail was that, although I wanted to use its Web-based interface, since that’s where all the innovation is, I also appreciate the fact that it provides access to my email via IMAP, for a local backup and in case I want to switch to some other email program in the future. (For some people, the capability to access Gmail from any computer with a Web browser is a big deal. Since I seldom use any computers but my own, this isn’t a significant advantage for me.)

Giving even more weight to my decision was the fact that, although I have my own mail server, I’d rather forward mail to Gmail and let Google’s engineers deal with keeping things running. Acting as my own email admin hasn’t been fun for years, between dealing with spam and the stress of being responsible for the email accounts of a number of local users.

So here’s my new philosophy of email, which has proven significantly less stressful than the last few years of using Eudora:

• I forced myself to let go of the need to file obsessively, via either filters or manual operations. I’m a professional, not the clerical help. I don’t even approve of the concept of clerical help — technology should eliminate the need for obsessive filing, and I’m letting Gmail do that for me now. This reduced a lot of stress, and after two years of usage, I haven’t yet missed my old filing system. Similarly, I’ve given up on managing an address book, which is possible because Gmail’s auto-fill of previously used addresses, both in the address fields and the search field, is wonderfully instant and accurate.

• Email is a constant stream, and while I want to be able to ignore it for a weekend, while I’m working, I want the option of seeing and responding to messages quickly and concisely. By eliminating the concept of checking mail, Gmail allowed me to escape the check/send cycle. Mail is either present in Gmail or it’s not; there’s no intermediate server where it could be. (In fact, because I still use Postini for server-side spam filtering for some tidbits.com addresses, this isn’t quite true.)

• While I don’t want to file messages, email should naturally collect into appropriate groups. Gmail does this brilliantly, automatically collecting messages with the same Subject lines into conversations, and making it trivial — far more so than in traditional programs — to collect messages associated with specific individuals or groups via a search.

Gmail Limitations -- Though I’m currently a big fan of Gmail, I think it’s important to acknowledge Gmail’s limitations up front. None of these are more than a minor irritation for me, but not everyone will agree.

First, some common concerns: privacy, security, and advertising. Although Google has a privacy policy that claims it won’t share information in unreasonable ways, the fact remains that Google stores all your email (as does any IMAP email provider). Since I’ve long subscribed to my mother’s advice not to say anything in email that I wouldn’t want on the front page of the New York Times, I’m not particularly concerned about Google having theoretical access to my email. Nor am I worried about Google somehow selling access to my mail; if such a thing ever happened and became known (and it would, given the scrutiny Google is under), it would cause irreparable damage to Google.

Also, with all your email online, all that protects it is your password (so pick a good one!). If that’s not sufficient for you, Gmail recently added two-step verification that requires a level of security beyond your password when your account is accessed from a new device. Lifehacker has a good explanation and tutorial, but beware that two-step verification can be a pain to use if you use other desktop or Web applications that access Gmail or other Google services and aren’t yet updated for two-step verification.

And the ads? Gmail analyzes every email message and displays contextual ads at the right edge of the message, ranging from the ridiculous to the occasionally creepy. Honestly, I seldom even noticed them, and now that I’ve installed the Rapportive plug-in, they don’t appear at all (see “Rapportive Plug-in Replaces Gmail Ads with Sender Info,” 27 March 2010). Similarly, Gmail’s distracting Web Clips, which display news items in a little box at the top of the Inbox, can contain ads; I just turn them off in the Web Clips screen of Gmail’s Settings (to access them, click the gear icon at the top of Gmail’s Web interface page and click Mail Settings in the menu that appears).

While Gmail’s Web interface is extremely good overall, there are certain areas where it falls down. Most notably, Gmail is occasionally slow to send a message or load a new one, showing a small progress message while I sit and stew. Most of the time it’s not an issue, which makes it all the more annoying on those occasions when it takes five to ten seconds to send a message or open a new one. Those are the only times I wish for a desktop application.

That’s not quite true. Gmail’s Web interface is designed for a single window, which is generally fine, since most email either doesn’t require reference to other messages or requires only checking back in the same conversation. But on those occasions when I need to refer back to a message in a separate conversation, it’s clumsy to pop an in-progress message into its own window so I can get back to the main Gmail window, perform a quick search, and refer to the older message while writing the new one. Gmail does offer both on-screen controls and keyboard shortcuts for generating separate windows, but it’s clearly of secondary importance and harder than it would be in a desktop application.

And of course, while you can download a local copy of your email via Apple Mail or any other IMAP client, you do have to do that if you want a backup of your mail. There’s no reason to believe Google would lose your mail permanently, but it’s always best to have a backup you control as well.

Most of the rest of Gmail’s problems are part and parcel with its innovations. For instance, as fabulous as conversations are the vast majority of the time, they sometimes get in the way. As an example, when we send out email about a new Take Control book, Tonya receives a number of email messages that all need individual attention. But because people often reply to incoming mail as a way of generating a new message, she’s often faced with a multi-message conversation where each message is actually an independent unit that’s harder to work with in the conversation than it would be on its own. (You can turn off conversation view entirely in Gmail’s Settings screen, but that’s overkill.)

Similarly, threads in mailing lists sort into conversations too, which is almost always a help. But if there’s private mail with participants of the thread, it can occasionally be confusing to have the private messages mixed in with the public ones. It would be nice if Gmail enabled us to explode any given conversation into its component messages.

There are a few areas where Gmail doesn’t compete with traditional email programs. For instance, when building spam-catching filters, it’s nice to have access to grep capabilities so you can match patterns of text. Gmail can’t do that, and in fact, all searches are word-based, so you can’t even do partial-word searches. Also frustrating is that you can’t search on arbitrary header lines, which can be useful for eliminating foreign language spam, for instance. Gmail does support searching on From, To, Cc, Bcc, Subject, and Delivered-To, along with dates and attachments, and realistically, I haven’t felt hampered by Gmail’s search limitations.

If you receive a ton of email, with lots of large attachments, it’s possible that the 7.5 GB of free space you get with a Gmail account might not be enough. However, at $5 per year for 20 GB (up to 16 TB), it’s hard to be too concerned about this.

Lastly, it’s not particularly easy to import old local email messages into Gmail. There is a Google Email Uploader for Mac, but it works only with Gmail within Google Apps, not with standalone Gmail accounts. The alternative is to connect your old email client to Gmail via IMAP (or import your old mail into Apple Mail or Thunderbird, which talk fairly well to Gmail via IMAP) and then copy messages manually, mailbox by mailbox. When I tried this with Eudora, I lost original dates on the imported messages, rendering it useless, and I’ve heard that it’s difficult to import significant quantities of mail at once, with the actions timing out and messages failing to transfer.

After considering the situation, I decided there was no significant win in importing my old Eudora mail. Eudora still launches and runs fine on my Mac Pro under Mac OS X 10.6.6 Snow Leopard, so when I need to find a really old message, it’s all still there. If Rosetta really does disappear in Mac OS X Lion, I may have to import all those messages into another program. Starting from scratch required some visits to my Eudora archive for the first month or two, and it took Gmail a short while to learn the email addresses of my most frequent correspondents. But the switch was otherwise entirely painless.

If nothing else, Gmail is free, offers excellent spam filtering, can accept mail forwarded from another account, and provides access to all your mail via POP and IMAP, so it’s easy to test.

In the next article in this series, I’ll explain in some detail how Gmail’s search-centric approach to email enables an entirely different technique of reading email (see “Zen and the Art of Gmail, Part 2: Labels & Filters”). Then, in “Zen and the Art of Gmail, Part 3: Gmail Labs,” I’ll delve into the many ways to extend and improve Gmail via Gmail Labs, and in “Zen and the Art of Gmail, Part 4: Mailplane,” I’ll look at the Mac program that makes using Gmail far more palatable than just having it in a Web browser tab.

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Gmail. In this second of a multi-part series, he explains how the fact that everything in Gmail is a search enables a Zen approach to email.Show full article

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After initially making the decision to try Gmail (see “Zen and the Art of Gmail, Part 1: Why I Switched”), I put a lot of thought into what I wanted to get out of email. This required some soul searching, since I’m generally an organized person who likes hierarchical filing systems. Spotlight has never helped me in the Finder, since I know where all my files are stored, and in Eudora, I had hundreds of carefully organized mailboxes that made searching merely a matter of looking in the right place.

But on the downside, my saved search strategy in Eudora was failing me (see “A New Way to Use Eudora,” 20 December 2004). The problem was that I had to do too much, in filing messages that couldn’t be filtered and marking messages that required later action in some way. The marked messages were the crux of the matter — labeling them Act On in Eudora was the kiss of death — I was almost guaranteed never to see them again. For a while I merely marked such messages as unread, so they’d nag me every day, but I quickly became capable of ignoring those as well, though their mere presence in my Unread Mail saved search made dealing with new messages all the more awkward.

After much consideration, I decided go for a Zen approach, and to see email as a river, where my goal was to do as little as possible to any given message as it flowed by. The first step in my journey was to set up labels and filters that would help manage much of my mail automatically.

Labels Are Searches -- Labels are one of the most powerful and subtle aspects of Gmail. Most people think of Gmail’s labels as being like folders in a traditional email program, but that’s missing two key points:

• A message in Gmail can have multiple labels assigned to it, whereas a message in a traditional email program can exist only in a single folder. A corollary to this fact is that every message in a traditional email program must live in a single folder; that is, everything must be filed. That’s not true in Gmail, where a message can have no label attached to it (it then shows up only in the All Mail collection).

• A label in Gmail is nothing more than a minuscule bit of metadata that can be used in a search. In essence, then, labels are saved searches, and are thus merely shortcuts. If you can identify all the messages from a mailing list with a filter (again, just a search), you can apply a label to those messages, even retroactively. But you may not need to, because you can always find exactly the same set of messages again later with a manual search.

If you think deeply about these two points, you realize that most filing that’s necessary in traditional email programs is a waste of time in Gmail. In those programs, you must file messages, because they have to live somewhere, and because searching isn’t fast enough or good enough to assemble a collection of related messages quickly. Neither of those problems exists in Gmail.

In contrast, you need to create a label for only three reasons in Gmail:

• You want to collect together messages that share little in common. For instance, I have an Order Receipts label that I apply manually to receipts from various Web merchants so I can verify credit card charges and check back on vendors I’ve used in the past. A filter assigns that label automatically to a few vendors that I patronize regularly, such as the iTunes Store and Amazon, but most receipts can be identified only by sight and labeled once they’ve arrived.

• You want to collect together messages that can easily be identified by a search for quick access as a group, and optionally as a way of removing them from your Inbox. Mailing lists are the canonical example here — you likely want to read the messages from a list all together, but that’s not necessarily true of all lists. In a traditional email program, you’d have to go to some lengths to display filtered mailing list messages along with other unread mail; in Gmail, you have to choose to separate mailing list messages via the Skip Inbox filter action.

• You want certain messages to be marked in the Inbox so you can tell at glance, for instance, that it’s a message to a mailing list rather than something sent only to you.

It may not seem as though this lets you create many fewer labels than you had mailboxes, but in my experience, it really does. In particular, I seldom create project-based labels, because I’m confident that I can find any message I need via a search for a sender or list address.

For instance, I could create a label to track messages related to my iPhoto Visual QuickStart Guide book for Peachpit, but that would basically entail collecting messages from my colleagues at Peachpit with peachpit.com or pearson.com email addresses, along with messages from the indexer, whose name I know. So there’s no significant win from labeling these messages; I don’t need to deal with them as a group, and if I did, a search would give me exactly the same results.

That’s not to say that other people don’t have the need to maintain project-based groupings of messages, and Gmail can handle that, just not any better than any other email program. You’d need to collect messages via filter (messages from a client’s domain, for instance) and via manual labeling (messages from a colleague about that particular project).

Labels have one small advantage over searches: message count. For unknown reasons, Gmail only estimates the number of results from a search, but displays the exact number of messages that have a certain label.

Sometimes, I’ll pass up a label in favor of a Quick Link, which is a Gmail Labs widget that puts a list of links in the left sidebar. I’ll talk more about Gmail Labs later in this series, but I like Quick Links a lot because it gives me fast access to a group of messages without making a label. Just like labels, Quick Links are saved searches, and can encapsulate anything you can search for, but they don’t apply any metadata to found messages. For instance, one Quick Link I use finds messages in TidBITS Talk or to our internal press release list that have also been marked as spam so I can identify any false positives.

Filters Are Searches -- Gmail has no lock on the concept that filters are searches — that’s how all email programs work. But it’s such an important point that I want to emphasize it.

Filters let you search for messages that match certain criteria: from a certain address, with a certain word or phrase in the Subject line, and so on. Once a message is caught by a filter, the filter can perform certain actions on it, the most important of which is to apply a label.

To be specific, filters can look for text in the From, To, and Subject lines, and anywhere else in the message, though Gmail unfortunately lacks the capability to search any arbitrary header line, like Content-Type or X-Sender. When looking for text in the body of the message, you can match messages that both contain certain words and don’t contain others, but there’s no grep searching or partial-word searches. You can also filter messages based on their attachments.

Once you’ve defined your criteria, the actions you can perform on a message are:

• Skip the Inbox (Archive it): All this does is remove the Inbox label. I use it heavily with non-essential mailing lists to keep them out of my Inbox.

• Mark as read: Since the unread status of a message is important to me, the only time I use this action is to mark messages from me to a mailing list as read. (Most of the time I don’t even see such messages, since Gmail usually doesn’t display messages you’ve sent to a list, knowing that the incoming message from you to the list would just duplicate the outgoing message already stored in the conversation. This is generally welcome, but can be annoying when testing or troubleshooting.)

• Star it: The star is equivalent to Apple Mail’s flag, and is a simple on/off way of marking a message. I use it manually to mark messages that need further action, so I don’t use it in any filters.

• Apply the label: Applying labels is the most common thing filters do; I have only one or two that don’t apply a label.

• Forward it to: Be very careful of filter actions that can send mail for you; if you need such a feature it’s here, but it’s awfully easy to have it go awry.

• Delete it: I would use this filter action only to clean up a large archive of mail; if I was receiving messages that I wanted to delete every time, I’d try to figure out some other way of stopping them.

• Never send it to Spam: Some mailing list messages can look an awful lot like spam; check this option to ensure that Gmail doesn’t accidentally mark a good list message as spam. I have to mark a few list messages as spam manually each month because of using this option, but that’s better than suffering false positives.

• Send canned response: This action, provided by Gmail Labs, is again the sort of thing I would be hesitant to use without very careful testing, since it’s easy to spew canned responses to the wrong people.

• Always mark it as important: This action tells Gmail’s new Priority Inbox feature that the message is important. I haven’t used it, since I want to tell Gmail manually when things are important, and Priority Inbox learns well from past actions.

• Never mark it as important: Also related to Priority Inbox, this one is more important from a filter standpoint, since you can use it to make sure that other filtered messages (such as automated messages and mailing list messages) never appear in your Priority Inbox.

Gmail’s filter capabilities are limited in comparison with traditional email programs, not surprisingly, since there’s less manipulation that can be done with messages on the Web — you can’t execute an AppleScript, for instance. (For that, you’d need to let a Macintosh email program access your Gmail messages via IMAP, which is totally possible.)

Where Gmail’s filter interface shines, though, is in showing you the results of a filter you’re creating on your current archive of email (with the Test Search button), and giving you the option of applying it to existing messages as well as future ones (with the “Also apply filter to X conversations below” checkbox in the final filter creation screen). That’s huge, because it means you can use filters for one-off actions like finding and deleting all the messages associated with a mailing list you’ve decided you don’t like.

Forget Inbox Zero -- Now that you understand how labels and filters work, let’s return to how I suggest you use them. The main use is to manage the flow of incoming messages, reducing the number that hit your Inbox to just those that you need to see as they arrive.

My goal with my Inbox is to read everything that comes into it, replying to those messages that require replies and labeling manually those very few messages that only I can identify. Thanks to the hundreds of email messages I receive each day, I need to filter non-essential mailing lists and various automated messages (Twitter follower notifications, Netflix shipping alerts, and so on, all of which receive an Automated Messages label) out of my Inbox. These filters apply the appropriate label and include the option to Skip the Inbox.

But I do want messages from key mailing lists, like the TidBITS staff list and the Take Control authors list, to appear in my Inbox, since they’re equally as important as messages sent only to me, and often more so. The filters that set labels for these mailing lists simply don’t use Skip the Inbox, so every message from the lists gets both the list label and the Inbox label.

Finally, of course, there are the messages sent directly to me from random people all over the globe. There’s no effective way to filter these messages in any way, and although I could label them after the fact, my Zen approach to email discourages that. The simple fact is that in over a year of use, I have yet to need such an arbitrary collection; a search has always produced the message I need.

The astute reader will note that most of my mail will continue to live in my Inbox, or, rather, will continue to keep the Inbox label. In other words, forget Inbox Zero. I have over 40,000 messages with the Inbox label, and you know what? It makes absolutely no difference in my usage, because Inbox is just another label, and there’s no reason to perform an additional action for every message to remove it. This bothers many people who want to simulate the email programs of yesteryear, so Google added an Archive button that, when clicked, removes the Inbox label. That’s all it does, and thus qualifies as entirely unnecessary work, since there’s no liability to leaving the Inbox label in place.

Not only do I file hardly any messages manually, I almost never delete messages. Gmail automatically deletes messages marked as spam after 30 days, but the only other messages I delete are test messages (TidBITS issues, Take Control orders, notifications from the TidBITS Commenting System) that I don’t need and that could confuse future searches.

You might think this is folly, since it would seem easy to lose unread messages among everything else in the Inbox — especially since Gmail cannot sort messages in any way other than by date. But in fact, there are two reasons this works: the search “is:unread is:inbox” and Google’s new Priority Inbox feature.

The “is:unread is:inbox” search shows all the messages with the Inbox label that are unread, ensuring that I can at any moment focus on just those messages. And remember the Quick Link widget I mentioned earlier? I’ve encapsulated that search into an Unread Inbox Quick Link that has become my default view on my Inbox.

I relied heavily on that search until Gmail gained Priority Inbox; now I use the search only to find messages that both Priority Inbox and I have failed to see when they were new.

Priority Inbox to the Rescue -- Priority Inbox is a relatively new feature for Gmail, and another example of how Gmail is rethinking email. You’re probably familiar with how spam filters can analyze messages and decide if they look like spam, based on other messages that you’ve marked as spam? Well, Priority Inbox works the same way, but instead of identifying spam, it identifies messages that are important to you.

How? Gmail just starts guessing as to what’s important and what’s not, and you correct it as it goes. Within a remarkably short time, you’ll find that the messages you most care about appear in your Priority Inbox, and the rest show up in an Everything Else list at the bottom of the Gmail window. If you ever want to see why Gmail thought something was important, just hover over the little yellow icon that indicates the message is important, or, if you’re in the message, click the Show Details link.

Priority Inbox is fairly malleable, in fact, providing up to four sections, the first three of which are configurable. For each of these, you can set Gmail to show messages in the Inbox that are Important and Unread, Important, Unread, or Starred, or you can have Gmail display the contents of a label in the section. For all four sections, you can choose how many messages should display.

I’ve configured Priority Inbox’s sections as follows. The first one shows Important and Unread messages, the second shows Starred messages (things I need to come back to), the third shows my Press Releases label (messages I want to scan, but don’t want cluttering my Inbox), and the fourth is Everything Else. I actually spend a fair amount of time in Everything Else, since new messages that aren’t deemed important appear there, as do important messages once I’ve read them.

What I’d really like to see from Priority Inbox is the capability to have Gmail automatically label messages based on previously labeled messages. That way I could train it to collect messages about certain topics or projects and have those added to automatically over time.

Shortly after I wrote that last paragraph, Google introduced a new Gmail Labs feature called Smart Labels that promises roughly what I want. Unfortunately, Smart Labels can assign only three hard-coded labels to messages: Bulk, Forums, and Notifications. Since my filters are far more specific, they’re more useful to me. If you were entirely new to Gmail, I could see trying Smart Labels for a while to see if it proved to be sufficient.

My Email Flowchart -- To summarize then, here’s how my email works. Messages come into Gmail. Filters assign labels to incoming messages from mailing lists, along with a few other predictable types of messages. Important mailing list messages retain the Inbox label so I see them sooner; secondary mailing lists lose the Inbox label. That all happens without me even noticing (unlike in traditional mail programs, which are always checking for mail and showing filtering status and whatnot).

To start reading mail, I just look at the top of my Gmail window, where the Priority Inbox’s Important and Unread section lists the most recent messages. I then click the first unread message and read it. From that point, there are only seven actions I might take on that message (listed in order of how often I perform them):

• Do nothing, merely absorbing the information in the message and its attachments. One nice touch in Gmail — many common attachment types can be viewed online without being downloaded and opened in another program. I can’t tell you how many random attachments I have cluttering my hard disk from my Eudora days.

• Reply to the message. Because Gmail always lumps messages with the same Subject line together, replies are stored with the messages they’re in reply to, making it easy to follow discussions as they evolve; I depend heavily on this feature.

• Mark the message as unread. Sometimes I want to pretend that I haven’t read a message. Perhaps I’m glancing at something just before leaving for an appointment, or it’s too near the end of the day to think of an appropriate response. Or, because I sometimes read email on my iPhone (where the mobile Gmail client is quite good, but can’t make up for the iPhone’s clumsy text entry capabilities), I often mark messages that need a real response as unread.

• Star the message, whether or not I’ve replied already. This is my marker that indicates “I should really do something based on the content of this message, so I’m going to mark it in such a way that I could theoretically find it in the future.” In reality, the star is my new kiss of death, and although I sometimes explicitly look at and deal with starred messages, it often turns out that I’ve already dealt with the issue or it has become irrelevant in the interim. So it goes.

• Apply a label manually, if it’s an order receipt or another type of message that can’t be identified by a filter for labeling. Again, I do this only occasionally, since it’s usually make-work.

• Click the Report Spam button, if the message slipped past both Postini’s server-side filtering and Gmail’s own very good spam filtering. Postini is now owned by Google, though I can’t tell how that affects spam filtering.

• Delete the message. I do this only occasionally, and only for test messages. I never use the Archive option in Gmail that removes a message from the Inbox, since there’s no benefit when clearing messages out of the Inbox ceases to be an amusing game.

Because the Report Spam and Delete buttons remove the Inbox label and apply the Spam and Trash labels, respectively, thus-labeled messages disappear entirely (since they no longer match the search), switching me to the list of unread messages again. Marking a message as unread also has the effect of switching back to the message list, which makes sense.

With all other actions — replying, starring, applying a label, and doing nothing — I follow that by pressing the keyboard shortcut — the k key — to move on to the next message, where I once again go through the simple steps. For most messages, I have only to decide if I wish to pretend I haven’t read the message yet, or if I need to reply. And in only a few situations, I also have to think about if I should mark the message for later dealing in some way, and if it needs additional labeling.

Every so often, I use my Unread Inbox Quick Link to display all the unread messages in my Inbox, regardless of their importance. That’s useful because every now and then an unimportant unread message can fall off the bottom of the chronologically sorted Everything Else list, and without this explicit check, I’d likely never see it.

That’s it for reading and replying. Composing messages is easy too, but the overall task is so simple that Gmail doesn’t have much room to improve on what traditional email programs do. It does an awfully good auto-complete as you type a few characters in someone’s name, and presents the list of possible matches sorted by how often you write to them. And of course, there are some useful enhancements available from Gmail Labs that help prevent addressing mistakes. That’s where we’ll turn in the next article (see “Zen and the Art of Gmail, Part 3: Gmail Labs”), after which we’ll look at Mailplane, the Mac application that breaks Gmail out of the browser (see “Zen and the Art of Gmail, Part 4: Mailplane”).

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Gmail. In this third of a multi-part series, he looks at how Google engineers have extended Gmail in a wide variety of optional — but sometimes very helpful — ways.Show full article

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In this series so far, I’ve explained features of Gmail that are standard (see “Zen and the Art of Gmail, Part 1: Why I Switched”) and “Zen and the Art of Gmail, Part 2: Labels & Filters”). But as much as I’ve liked using Gmail, the fact that it has met my needs in large part has been due to the optional enhancements provided by Google engineers via Gmail Labs. I presume these are the sort of features that Gmail’s product managers consider unnecessary for most users, but they’re made available to anyone who wants them, and some are essential to my workflow.

To access Gmail Labs, click the gear icon at the top of Gmail’s Web interface page and click Labs in the menu that appears. (For Google Apps accounts, there’s a Settings link at the top instead of the gear icon.) Then scroll down through the long list of items, clicking the Enable radio button for any that look interesting. I recommend being somewhat conservative in how many you enable at a time, since a flaky Gmail Labs feature can in theory cause Gmail to fail to load. I won’t attempt a laundry list, but here are the ones that I find make an actual difference to my Gmail use, in rough order of importance.

Quote Selected Text -- I consider this Gmail Labs feature essential for cutting some replies down to size. Much of the time there’s no need to quote an entire original message in a reply, and with this feature enabled, you can select just the text you want quoted before replying. This feature is commonplace in traditional email programs, and I would miss it horribly if it weren’t available in Gmail.

Undo Send -- One of the things I liked about Eudora was that I could queue messages for later delivery, which would happen either on my next mail check, or when I manually released them. It was entirely common for me to remember something I wanted to add to a queued message, so I appreciated that approach, even though it created a little more work.

Gmail, like many other email programs, lacks the concept of queuing outgoing messages, instead offering only a Drafts mailbox for in-progress messages that you haven’t yet sent. That’s not good enough; I need to be able to add to a message that I previously thought was done, and the Undo Send feature of Gmail Labs gives me that.

Once enabled, it displays an Undo link on the screen next to where Gmail reports “Email Sent.” Click it within 30 seconds (configurable in the main Settings screen), and Gmail moves the message (which hasn’t really been sent yet) back into Drafts and lets you edit it again. I use it regularly.

Quick Links -- I really like the Quick Links widget, which enables me to create a single-click link to any bookmarkable URL in Gmail, most notably unread messages in my Inbox. So, anything you can encapsulate in a search, such as the following, can be turned into a link for instant access.

• is:unread in:inbox — This displays all unread messages in the Inbox.

• in:spam (label:tidbits-talk OR label:press-release) — This one looks for messages sent to TidBITS Talk or our press release reflector that have been marked as spam — every now and then Gmail produces a false positive. I scan this occasionally and mark good messages as not spam.

• from:(tonya@tidbits.com OR tc-comments@tidbits.com) -{label:tc-order label:automated-message} — This one shows all messages from Tonya, eliminating some automated messages that also send mail from tc-comments@tidbits.com.

One tip: Complex searches in Gmail are easier to build if you first click Show Search Options (in tiny text to the right of the search field). Then build your search, make sure it finds the right messages, and copy the search phrase from the “Search Results for:” line to the left of Gmail’s main interface buttons. Then paste that into the normal search field and make your Quick Link. If you make a Quick Link with Search Options showing, it will show every time you use the Quick Link, which is a waste of screen real estate.

Alas, Quick Links can’t have keyboard shortcuts, which would be helpful.

Navbar Drag and Drop -- Gmail puts quite a number of items in the left-side navigation bar, but they aren’t always in the order you want. With this Gmail Labs feature, you can rearrange them, at least somewhat. I like to put Quick Links near the top, but it often moves down on its own for unknown reasons.

Multiple Inboxes -- Like Priority Inbox, the Multiple Inboxes widget in Gmail Labs tweaks Gmail’s default list of messages, offering you up to five additional boxes that you can use to display the results of any search. (Remember, everything is about search.) Of course, the most likely searches are for labels, but you can display anything you can find. You can set how many messages appear in the boxes, though they all use the same number.

The various boxes can be displayed below, above, or to the right side of the main Inbox. I could see above being useful for particularly important messages, and I prefer below, but because the right-side display shrinks the Subject area of the message list, it would be helpful only with a very wide window.

You configure the searches for Multiple Inboxes in its own settings screen, accessible from a link added to the others at the top of the main Settings screen.

Unfortunately, Priority Inbox overrides Multiple Inboxes, so to see the Multiple Inboxes display, you must click the Inbox link in Gmail’s left-hand nav bar instead of the Priority Inbox link. Since Priority Inbox came out, I don’t use Multiple Inboxes nearly as much.

Previews in Email -- A number of Gmail Labs features enhance Gmail by embedding content right in the message, based purely on links included in the message. So, if a friend sends you a link to a set of Flickr photos, the Gmail Labs feature lets you view see previews of the photos right in Gmail, without having to bounce out to Flickr.

Currently, you can get previews for Flickr, Picasa, Google Docs, Google Maps, Yelp listings, and even Google Voice messages (so you can play your Google Voice voicemail right from the email notification). YouTube previews used to be available via a Google Labs feature, but are now built into Gmail by default.

Smart Addressing -- A pair of Gmail Labs features make Gmail the best email program I’ve seen for helping the user avoid addressing mistakes. Once you add one or more recipients to a message, “Don’t forget Bob” enables Gmail to suggest other people, based on groups you have sent email to in the past. And “Got the wrong Bob?” alerts you when you address a message too quickly and accidentally send to Bob (your boss) rather than Bob (your friend). It kicks in only once you’ve added more than two recipients (since it needs the context of groups you’ve sent email to in the past to guess that you might have the wrong Bob). For more information, see “Gmail Further Foolproofs Group Emailing ” (15 October 2009).

Google Calendar Gadget -- Since I have full access to my calendar in BusyCal on my Mac at all times, and reminders from it and on my iPhone, Google Calendar isn’t that important to me. But since we use Google Calendar as the intermediary for sharing certain calendars via BusyCal, I’ve added the Google Calendar widget to Gmail as well, so I see a little box showing the next couple of events in Gmail’s left-side navigation bar.

Advanced IMAP Controls -- Although I read my mail in Gmail’s Web interface, I also back it up by retrieving it in Apple Mail via IMAP. That way, should something awful happen to Google or my mail in particular, I have a local copy that’s backed up along with all the rest of my data. This Gmail Labs feature makes working with IMAP a bit easier. My understanding is that Gmail’s IMAP is, shall we say, kind of weird, since it has to map labels to IMAP folders (meaning that a message can appear in multiple IMAP mailboxes). For more information, see Joe Kissell’s essential article on the topic, “Achieving Email Bliss with IMAP, Gmail, and Apple Mail” (2 May 2009).

Canned Responses -- This feature attempts to mimic Eudora’s stationery feature, at least as far as the boilerplate text goes (Eudora’s stationery could include message header information as well). Although I like the idea of having canned responses, in the real world, I don’t use it much, and I use it only manually since I don’t trust software to send mail for me automatically. But that’s just me. Of course, you could also use something like TextExpander or Keyboard Maestro for this functionality, though such utilities don’t appear within Gmail’s interface.

Add Any Gadget by URL -- I don’t use this Gmail Labs feature, but I like the idea of it, and I tried using it briefly to put a Twitter gadget in Gmail’s left-side navigation bar. There are oodles of Google gadgets, which are roughly similar to Dashboard widgets. The only problem is that a lot of them are bad, and not all display well in the limited width of Gmail’s navigation bar.

While Gmail Labs widgets can go a long way toward improving the overall Gmail experience, there’s one more thing you can — and should — do to make Gmail into a first-class citizen on your Mac. For that, you’ll need to use the Mailplane application to free Gmail from the confines of your Web browser, and I’ll look at Mailplane in the next installment in this series (see “Zen and the Art of Gmail, Part 4: Mailplane”).

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Gmail. Although he likes Gmail’s Web interface, since that’s where most of the innovation lies, he uses Mailplane to enhance the experience on the Mac.Show full article

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So far in this series, I’ve said a great deal about Gmail’s innovations, which are available only through its Web interface. (If you haven’t seen the earlier articles, check out “Zen and the Art of Gmail, Part 1: Why I Switched,” “Zen and the Art of Gmail, Part 2: Labels & Filters,” and “Zen and the Art of Gmail, Part 3: Gmail Labs.”

But there’s a problem with a Web-based interface, which is that it requires a Web browser. Don’t get me wrong, I have nothing against Web browsers for browsing the Web, but for the most part, Web browsers do a mediocre job of hosting Web applications like Gmail. That’s because we often think of and use Web applications in much the same way we think of and use desktop applications, and mixing them in with static Web pages that we open and close with abandon can be a recipe for frustration.

Just think about accessing your email program. You might do so via an icon in the Dock, or via LaunchBar, or some other common mechanism. But if your email program is just a bookmark to a Web page, any of those methods will create a new Gmail tab in your browser, and you’ll get another new Gmail tab every time you click it (this isn’t universally true; Safari 5 sometimes reuses a tab, and Firefox 4 now features app tabs; see “Firefox 4 Improves, But Not Radically,” 2 April 2011). So unless you switch to Gmail by switching to your Web browser and then finding the open Gmail tab, you’ll be constantly opening and closing Gmail tabs, which is an annoying waste of time.

One solution is a site-specific browser like Fluid (which uses WebKit, the technology Safari is based on) or WebRunner (which replaces Prism and essentially encapsulates Firefox). These can effectively turn any Web site into a standalone application that appears in your Dock and doesn’t mingle with other Web pages. But my experience with both is that while they work for some sites, there are plenty of sites where they either don’t work or are clumsy to use for a variety of reasons, including authentication issues, tab-handling, lack of support for plug-ins or extensions, and so on.

Prepare for Takeoff -- Luckily, there’s a much better solution: Mailplane, a highly site-specific browser that’s just for Gmail. Mailplane is based on WebKit, like Safari, but developer Ruben Bakker of Uncomplex has done a truly amazing job of turning what is essentially a Web browser into a real Macintosh application.

Uncomplex has a page comparing Mailplane to using Gmail in a browser, and I won’t list out the many ways in which Mailplane outdoes the browser experience. But I do want to touch on those that I’ve found to be a big win in my everyday use.

Most important is of course the separation of Gmail from the rest of my browsers and tabs. That lets me map the F3 key on my keyboard to Mailplane, something I’ve done for my email program for more years than I can remember. And as a real desktop application, Mailplane can set itself as the default mail application on the Mac, accepting clicks on mailto links and other actions that would normally be sent to Mail or Eudora or whatever.

I also like being able to drag files onto the Mailplane window or its icon in the Dock to attach them to a message (Google has now made it possible to attach files via drag-and-drop into the Gmail window in Web browsers, but that wasn’t true when I started using Mailplane).

Mailplane simplifies certain things that are tough in browsers, such as maintaining multiple accounts. Until August 2010, in a browser, if you wanted to switch among multiple Gmail accounts, you had to log out of the current one and log into the second one, reversing the process to go back. Although Google now allows multiple account sign-in, the process is still clumsier than with Mailplane, which enables quick switching among accounts with a simple double-click in the Accounts drawer.

Because I test a lot of software and report on behavior to developers and designers, I adore Mailplane’s built-in screenshot capability. While writing a message, I can click the Screenshot button in Mailplane’s toolbar and take a screenshot of a selection, a window, or an entire screen. Once I’ve made the appropriate selection, Mailplane takes the screenshot and attaches it to the message with no more interaction (and I don’t have to throw out any temporary screenshot files later).

Although Mailplane provides Mac-like keyboard shortcuts for a slew of Gmail actions, I’ve intentionally avoided them in favor of Gmail’s own internal shortcuts (press ? to see a cheat sheet of all of them, and check out Lifehacker’s “Become a Gmail Master Redux” article for suggestions on using them). That’s because, as much as I like Mailplane, I’m a keyboard-focused user, and I don’t want to become dependent on Mailplane’s version of Gmail’s keyboard shortcuts for those times when I do use Gmail in a Web browser. But I could see some people really appreciating the familiar keyboard shortcuts.

Mailplane also integrates with Growl, notifying me of new messages as they come in. But it’s not just any message that comes in; Mailplane triggers Growl notifications only for messages that hit my Priority Inbox, so the tons of automated messages and mailing list discussions that flow into my mailbox don’t bother me.

Finally, and this is an improvement over only the generic site-specific browsers, Mailplane supports a few Gmail plug-ins: Rapportive, TrueNew, and 0Boxer. Rapportive is wonderful, since it replaces Gmail’s ads with information about your email correspondents (see “Rapportive Plug-in Replaces Gmail Ads with Sender Info,” 27 March 2010). TrueNew is relatively trivial, but shows the unread count for your Inbox and, separately, the number of new messages since your last interaction with your Inbox (I’m not sure this is working since Gmail’s last minor revision). And 0Boxer is essentially a game where you score points by reading and replying to email; you can compare yourself to friends or to the world at large. It was amusing briefly, but after a while, it wasn’t worth the interface space at the top of the window.

While it’s great that Mailplane supports these plug-ins, plug-in support is actually something that points toward using Gmail in a normal browser, and mostly in Firefox or Chrome. That’s because there are a bunch more Gmail-based Web apps and plug-ins that work only in browsers. Of course, many of them attempt to provide features that Mailplane already does better, but there are some I’d love to use.

For instance, there’s Boomerang, which lets you schedule when messages should be sent and can automatically remind you if you haven’t heard back from someone in a couple of days. (Note that Mailplane has now added support for Boomerang; see “Mailplane 2.3.1 Adds Support for Boomerang for Gmail,” 11 April 2011.) And ActiveInbox gives Gmail a Getting Things Done-style makeover. Then there’s socialGmail, a Chrome-only plug-in that displays avatar photos next to senders in Gmail message lists. And although CloudMagic currently requires that you allow IMAP access to your All Mail label (which causes normal IMAP clients to download a lot of unnecessary duplicates), it’s an interesting Gmail plug-in that provides instant searching no matter where you are in the Gmail interface. I could go on, but I think you get the point — there are ways of extending Gmail that just aren’t available until and unless Uncomplex can build them into Mailplane.

In the end, despite my occasional yearning for one of these Web apps or plug-ins, Mailplane provides so many features that I rely on every day that I never end up using Gmail in a normal Web browser for more than testing. It’s well worth the $24.95 purchase if you use Gmail on a Mac.

What about Sparrow? -- There’s been some excited chatter about a new Gmail-focused application called Sparrow. I’ve looked at Sparrow, and while I’m tremendously happy to see Mac developers building a pretty interface on top of Gmail, Sparrow simply doesn’t act enough like Gmail to make it worthwhile for me. That may change as the program evolves, but for now I have these problems with Sparrow.

• While Sparrow does support Gmail conversation view, it reverses the order of the messages, showing the most recent at the top, which is just plain wrong. For instance, if you come into a mailing list thread after messages have arrived, you have to read it from the bottom up.

• Although Sparrow can hide quoted text, it doesn’t do nearly as good a job as Gmail at minimizing reply attributions and signatures, resulting in a messy reading view.

• In Sparrow, you can see your labels only by clicking a pop-up in the lower-left corner; I’d like to be able to pin specific labels to the left sidebar, which has a lot of unused space.

• Speaking of unused space, Sparrow takes the idea of providing white space to an extreme, which forces a lot of unnecessary scrolling in both the message list and the conversation view.

• Sparrow supports some of Gmail’s keyboard shortcuts, but not all of them, which can be a little confusing if you’re trying to switch back and forth.

• Following in the steps of the Twitter app, Sparrow eschews standard interface elements, and a lot of controls, even including such standards like scroll bars, appear only when your cursor is in the right place. I’m all for user interface experimentation, but not when it hurts usability and discoverability, as do a number of Sparrow’s design decisions.

• Sparrow seems notably slower than Gmail at loading messages, so I see its spinning progress wheel fairly frequently. Ideally, a desktop email client would be faster than a Web-based app.

In short, I think Sparrow is simply not sufficiently baked yet for anything but minimal email use. Nonetheless, I have high hopes for it, since it’s the only desktop application I’ve seen yet that acknowledges and attempts to replicate Gmail’s innovations.

Gmail on iOS -- One thing I haven’t mentioned much is using Gmail on the iOS devices, in part because although I do occasionally read email on my iPhone, I don’t do it much. The main thing to consider is that when you’re using an iOS device, you can access Gmail either using the Mail app using Gmail’s IMAP interface, or using Gmail’s mobile Web interface using Safari. There are also a number of apps, such as Mailroom, iGmail, and MultiG, that encapsulate Gmail’s mobile Web interface in a standalone app, much like Mailplane does on the Mac. There’s nothing wrong with them, but the few features they add — like multiple account support — aren’t generally those that I need on my iPhone or iPad.

Although I’ve set up Apple’s Mail app to access my Gmail, since it’s a standard IMAP client with none of Gmail’s innovations (like conversation view, great searching, and so on), for those times when I do want to access Gmail on my iPhone or iPad, I always go to the mobile Web interface.

Google has done a bang-up job for both the iPad and iPhone/iPod touch, creating custom interfaces that react well to the available screen size while providing most of the standard features you’re used to having in Gmail. In particular, I appreciate the conversation view, since it turns reading threads into a simple scroll action, and the capability to search across all my email, since I often look for directions or an address from my email when I realize I don’t quite know where I’m going while driving. The iPhone/iPod touch version of the interface uses multiple screens, one for listing messages and another for displaying them, so there’s a bit more back and forth than with the iPad interface, which can display the message list at the same time as a message.

Honestly, though, the main thing I do with Gmail’s mobile clients is read messages, marking them either as unread or starred for dealing with later once I’m back on the Mac with a real keyboard. I haven’t tried doing all my email on the iPad with an external keyboard; it should be pretty reasonable, but I haven’t yet had the need.

Getting into the Gmail Mindset -- I won’t pretend that switching to Gmail is a trivial step to take, but if you don’t get bogged down in the morass of moving all your existing email and contacts into Gmail and replicating every system you had in your previous email client, you can turn Gmail into a lean, mean, email machine with a little help from Mailplane. I’m not just saying that, I’m living it, and I get one heck of a lot of email. So while I won’t pretend that Gmail is the right email solution for everyone, I have no trouble recommending that anyone who is not happy with their current setup give it a try.

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The latest minor update to the Gmail client Mailplane adds support for the Boomerang plug-in and service that provides scheduled message delivery and automatic followup reminders if you don’t hear back from a correspondent.Show full article

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It may not sport a major release number, but the update to Gmail client Mailplane 2.3.1 is actually quite significant. It provides a few minor bug fixes and has only two new features, the first of which (compatibility with Mac OS X Lion) isn’t terribly interesting for most of us. But the second significantly enhances Gmail usage by building in support for the free Boomerang for Gmail plug-in and service, which has previously been available only for Firefox and Google Chrome users. (To enable the plug-in, in Accounts pane of Mailplane’s preferences, click the Plug-Ins button and select the “Load Boomerang plugin (by Baydin)” checkbox.)

Boomerang for Gmail brings back to Gmail a Eudora feature that, if not unique, was at least unusual: scheduling of message delivery. (Apple Mail lacks scheduling, but a free AppleScript-based solution makes it possible to queue messages for later delivery.) Sometimes you want to queue a message up now, but not have it sent for an hour or a day or a week. For instance, if I’m sending someone a huge file via Dropbox, it takes some time for Dropbox to upload the file and make it available, but I don’t want to have to check back on Dropbox in an hour to see if it’s done, and I don’t want to tell my recipient to wait an hour from the time I sent the message to see if the file is there. Instead, I tell Boomerang to send the message in an hour, when I’m certain the file will be available. I also sometimes queue up birthday wishes or other time-specific messages so I can write them in advance and have them delivered at an appropriate time. You can even edit queued messages, though the process requires canceling the action, editing the message, and rescheduling.

But Boomerang goes beyond just bringing back a feature missed in Eudora. Most notably, it solves the problem of remembering to follow up with people who haven’t responded to an important message. You can set Boomerang to remind you in a user-specified amount of time if you haven’t heard back from the person, or even if you have. This is huge, because now you don’t have to make a to-do item to follow up with someone — Boomerang does that for you.

Finally, sometimes you may receive an important message that you need to deal with, but not right away. You could star the message, or apply a label that identifies it, but those require you to notice the message in the future when the time comes to deal with it. Instead, you can just tell Boomerang to take the message out of your Inbox right away and bring it back at a specified time and date. It can optionally make the returned message unread, starred, appear at the top of your Inbox, and labeled as “Boomerang.”

If the text of a message contains a date or time, Boomerang even automatically suggests an appropriate time to return it. Boomerang’s creators, Baydin, note that if a message suggests a meeting at 4 PM on Thursday, Boomerang will automatically offer to return the message 2 hours before so you have time to prepare. I haven’t found this useful, personally, but perhaps I don’t do enough scheduling in email.

As you schedule messages for later delivery and set Boomerang to remind you about messages, those actions accumulate in Boomerang’s dashboard, accessible from a Boomerang link at the top of the Gmail window. You can reschedule messages or send/return them right away, if you like.

The only awkward thing about Boomerang is that it works its magic by maintaining several Boomerang-specific labels and sending you additional messages, which have the effect of bringing the associated Gmail conversations back to the top your Inbox. It feels a little clumsy, but the approach is effective.

Taken together, these scheduling features make Gmail even more useful in ways that email clients simply haven’t done in the past. It’s a shame too, since capabilities like message scheduling, followup reminders, and delaying of messages aren’t magic, and could easily work their way into other programs. (In fact, if you use Windows at work, there’s an Outlook version of Boomerang too.) But since no Mac clients have done this sort of thing, Boomerang, and Mailplane’s new support for it, is just another reason why I like Gmail so much (see our series “All About Gmail” for details).

Boomerang is free to use, but the company makes it possible to buy a subscription if you find it useful; currently, there are no different features for subscribers. Mailplane 2.3.1 costs $24.95 new; the update from previous 2.x versions is free.

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